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Cypresswood Houses for Rent

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  • /15

    $1,550 per month

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • House for Rent

    2648 Whispering Trails Dr, Winter Haven, FL 33884

    Please note that the advertised price may exclude additional fees. These include a mandatory $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; fees for amenities like smart home or internet service; and optional conditional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99), pet fees/rent, or pool

    2648 Whispering Trails Dr, Winter Haven, FL 33884
  • /14

    $1,200 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    2924 Whispering Trails Dr, Winter Haven, FL 33884

    Some pictures are virtual furniture. Modern Studio 1-Bedroom, 1 bath rental, – All Utilities Included! This Next Gen-style unit features a private entrance, walking closet, private screen porch, small kitchen, laundry, and private parking. Enjoy A/C, high-speed internet, electricity, water, trash, channel and yard care—all included in rent. Located in a quiet gated winter Haven community with

    maritza monzon INTERNATIONAL EXECUTIVE REALTY

    2924 Whispering Trails Dr, Winter Haven, FL 33884
  • /16

    $1,859 per month

    • 4 Beds
    • 2 Baths
    • 2,237 Sq Ft
    • House for Rent

    3013 Whispering Trails Dr, Winter Haven, FL 33884

    Featuring a sparkling community pool! This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,237 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon

    3013 Whispering Trails Dr, Winter Haven, FL 33884
  • /15

    $2,165 per month

    • 5 Beds
    • 3 Baths
    • 2,150 Sq Ft
    • House for Rent

    2037 Whispering Trails Blvd, Winter Haven, FL 33884

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    2037 Whispering Trails Blvd, Winter Haven, FL 33884
  • /16

    $1,705 per month

    • 3 Beds
    • 2 Baths
    • 1,303 Sq Ft
    • House for Rent

    3119 Whispering Trails St, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    3119 Whispering Trails St, Winter Haven, FL 33884
  • /35

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • House for Rent

    677 Augusta Rd, Winter Haven, FL 33884

    Welcome to your dream rental home in the prestigious guard-gated community of Cypresswood Golf and Country Club, where luxury living meets resort-style amenities. Nestled within this exclusive enclave, this meticulously crafted 3-bedroom, 2-bathroom home offers an unparalleled lifestyle experience. Upon entering, you're greeted by an inviting ambiance accentuated by high-end finishes and tasteful

    Kayly Malinas JOHN WOOD REALTY, INC.

    677 Augusta Rd, Winter Haven, FL 33884
  • /17

    $2,395 per month

    • 5 Beds
    • 2.5 Baths
    • 2,215 Sq Ft
    • House for Rent

    640 Grove St, Winter Haven, FL 33884

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    640 Grove St, Winter Haven, FL 33884
  • /8

    $2,050 per month

    • 3 Beds
    • 2 Baths
    • 1,268 Sq Ft
    • House for Rent

    2893 Whispering Trails Dr, Winter Haven, FL 33884

    Modern, elegant and functional: this single residence seamlessly blends the latest in design and technology. Enjoy kitchen, bright and open living spaces, a home office ready for remote work, and privileged access to gated community amenities with a pool. In addition, it features installed solar panels, providing energy savings and a more sustainable lifestyle. Perfect for dynamic families,

    Dailey Duarte Mendez LA ROSA REALTY LLC

    2893 Whispering Trails Dr, Winter Haven, FL 33884
  • /20

    $1,989 per month

    • 4 Beds
    • 2 Baths
    • 2,203 Sq Ft
    • House for Rent

    2665 Whispering Trails Dr, Winter Haven, FL 33884

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,203 square feet, this well-maintained home offers a high standard of

    2665 Whispering Trails Dr, Winter Haven, FL 33884
  • /40

    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 1,503 Sq Ft
    • House for Rent

    800 Overlook Grove Dr, Winter Haven, FL 33884

    3/2 2 car garage located in quiet neighborhood on a culdesac, new tile floors, new interior paint. Ready to move in home comes with many upgrades from the original model which include upgraded exterior stone and coach lights, radiant barrier in attic, Spacious master bedroom provides a nice retreat as well as large master bath with dual vanities, whirlpool tub and walk-in shower. Neutral colors

    Oscar Fonseca JEMCO REALTY & PROPERTY MANAGEMENT

    800 Overlook Grove Dr, Winter Haven, FL 33884
  • /37

    $1,995 per month

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • House for Rent

    668 Grove St, Winter Haven, FL 33884

    Enjoy living in this beautiful one-story home in the Inman Groves Community. The home features 4 bedrooms, 2 baths, with an open floor plan. The floor is all tile, the kitchen has all brand new, stainless-steel appliances and 42” cabinets, and a 2-car garage. A large master suite with a shower, all carpet in bedrooms, and a laundry room with a washer/dryer. The home is approximately 1853 sq ft of

    Amanda Yuan MULTI CHOICE REALTY LLC

    668 Grove St, Winter Haven, FL 33884
  • /16

    $2,600 per month

    • 5 Beds
    • 2.5 Baths
    • 2,254 Sq Ft
    • House for Rent

    930 Cattleman St, Winter Haven, FL 33884

    Welcome to 930 Cattleman St, located in the charming community of Inman Groves in Winter Haven, FL. This spacious Boston model by Lennar offers an ideal blend of comfort, functionality, and modern living. Boasting 5 generously sized bedrooms and 2.5 baths, this two-story home is perfect for families seeking space to grow or investors looking for strong rental potential. The thoughtfully designed

    Carlos Lopez Cadena EXP REALTY LLC

    930 Cattleman St, Winter Haven, FL 33884
  • /37

    $1,875 per month

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft
    • House for Rent

    4907 Summerfield Cir, Winter Haven, FL 33881

    Welcome to your new home at 4907 Summerfield Circle Winter Haven, FL 33881!Walk into this 3 bed 2 bath charming home and the first thing you'll notice is the abundance of natural light shining into the kitchen-to-family room combo. The kitchen offers ease & accessibility with all the major appliances including a dishwasher. The master suite is a dream come true with all the storage space

    Marilyn Kuczynski FLORIDA HOMES SALES & MANAGEMENT LLC

    4907 Summerfield Cir, Winter Haven, FL 33881
  • /17

    $1,795 per month

    • 3 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • House for Rent

    2049 Whispering Trails Blvd, Winter Haven, FL 33884

    Nice single-family home with 3 beds and 2 baths for rent in Winter Haven, open floor plan ready to move in, Washer and Dryer included.Don't miss out on the opportunity to make this beautiful unit your new home. Contact us today to schedule a showing!FCG REALTY residents are enrolled in the Resident Benefits Package (RBP) which includes a convenient option for renters insurance, HVAC

    Amber Madera FCG REALTY

    2049 Whispering Trails Blvd, Winter Haven, FL 33884
  • /30

    $2,450 per month

    • 5 Beds
    • 2.5 Baths
    • 2,254 Sq Ft
    • House for Rent

    1454 Austin Terrace, Winter Haven, FL 33884

    Make Winter Haven your new home. In Peace Creek Reserve, a master-planned community along a beautiful creek, this Edison home offers an open layout that integrates the kitchen, living room, and dining area and extends to the patio for outdoor enjoyment. Upstairs, five bedrooms surround a versatile loft (home office, study, or game room). The master suite offers a walk-in closet and en suite

    Carla Moreno Pineda EXP REALTY LLC

    1454 Austin Terrace, Winter Haven, FL 33884
  • /40

    $1,700 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    2956 Whispering Trails Dr, Winter Haven, FL 33884

    NEW IMPROVED PRICE for this 3 Bedroom, 2 Bathroom Home for rent in a Gated Community, just minutes from Legoland! This 1,500 sq. ft. rental home is ready for its new tenant(s)! Nestled in the highly desirable Whispering Trails community, this property offers a spacious open layout with a split floorplan, spacious living room, and a large kitchen featuring an oversized island and breakfast

    Kim Connahey HOUSE OF GLASS REAL ESTATE PM

    2956 Whispering Trails Dr, Winter Haven, FL 33884
  • /15

    $1,895 per month

    • 3 Beds
    • 2 Baths
    • 1,998 Sq Ft
    • House for Rent

    553 Saint Andrews Rd, Winter Haven, FL 33884

    This three bedroom, two bathroom home is located in the gated Cypresswood golf subdivision. Enjoy the numerous HOA amenities, including a private gated community entrance with 24/7 guard, pool, fitness center, tennis courts, and golf. Home features a split floor plan, updated kitchen with stainless steel appliances and a gas range, brand new carpet in bedrooms, an enclosed sunroom that overlooks

    Sharon Billups SKYELINE REALTY LLC

    553 Saint Andrews Rd, Winter Haven, FL 33884
  • /16

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,511 Sq Ft
    • House for Rent

    2700 Crump Rd, Winter Haven, FL 33881

    Lakefront Living at Its Finest!Discover the perfect blend of comfort, convenience, and stunning natural beauty with this 3-bedroom, 2-bath home located on the highly sought-after Lake Hamilton. This property offers unbeatable location — just minutes from shopping, dining, and entertainment, yet far enough to enjoy peace and privacy away from the city bustle.Recently updated, this home delivers

    Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

    2700 Crump Rd, Winter Haven, FL 33881
  • /12

    $2,200 per month

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • House for Rent

    3240 Country Walk Club Cir, Winter Haven, FL 33881

    Brochure Available, Docs Available, Floor Plan Available

    Moises Dominguez, LLC TBO REAL ESTATE PARTNERS INC

    3240 Country Walk Club Cir, Winter Haven, FL 33881
  • /3

    $3,400 per month

    • 5 Beds
    • 3 Baths
    • 2,845 Sq Ft
    • House for Rent

    740 Grove St, Winter Haven, FL 33881

    Nestled in the serene location of Winter Haven; beautiful house conveniently located near Lego Land. 5 bedrooms, 3 bathrooms, 2-car garage, stainless steel appliances. Fenced-in backyard offering space and privacy. Includes smart home technology so that you can connect to your home via smartphone. Enjoy Winter Haven's main attractions and sights such as boating on the Chain of Lakes and Antique

    Claudia Pulgarin Capital Nest Realty, LLC

    740 Grove St, Winter Haven, FL 33881
  • /2

    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,690 Sq Ft
    • House for Rent

    3268 Country Walk Club Cir, Winter Haven, FL 33881

    Discover this charming 3-bedroom, 2-bath single-family home located in the desirable Country Walk community of Winter Haven. This property offers comfort, style, and a prime location. Its open-concept design features ceramic tile and carpet flooring, solid surface countertops, energy-efficient windows, and an inside laundry room. The primary suite includes a spacious walk-in closet and a private

    Arlenys Oviedo EXP REALTY LLC

    3268 Country Walk Club Cir, Winter Haven, FL 33881
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